title: Asymmetric solid-phase alkylation of ketones immobilized via SAMP hydrazone analogue linkers.
abstract: The preparation and application of new solid supports with chiral linkers, analogues of SAMP hydrazine on solid-phase, are described. The supports were used for immobilization of ketones (diethylketone, cyclohexanone, 4- tert-butylcyclohexanone), and diastereoselective alkylation of formed chiral ketone hydrazones. The enantiomeric purities of cleaved alpha-alkylated chiral ketones ranged from 10 to 73%. The use of chiral lithium amides for metalation of hydrazones of t-butylcyclohexanone increased the enantiomeric excess of the alkylated product by 25-47%.
authors.affiliation: Institute of Chemistry, University of Bialystok, ul. Hurtowa 1, 15-399 Bialystok, Poland. lazny@uwb.edu.pl
authors.forename: Ryszard
authors.initials: R
authors.lastname: Lazny
authors.forename: Aneta
authors.initials: A
authors.lastname: Nodzewska
authors.forename: Beata
authors.initials: B
authors.lastname: Zabicka
mesh_terms: D000478:Alkylation; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D010663:Phenylmercury Compounds / Q000737:chemistry
chemical_list: D003432:Cross-Linking Reagents; D006835:Hydrazones; D007659:Ketones; D010663:Phenylmercury Compounds; C036235:4-(4-sulfophenylazo)-2-mercuriphenol